DE3686247T2 - Mischung von monoazofarbstoffen und verfahren zuem faerben von polyester fasern unter verwendung derartiger farbstoffmischungen. - Google Patents
Mischung von monoazofarbstoffen und verfahren zuem faerben von polyester fasern unter verwendung derartiger farbstoffmischungen.Info
- Publication number
- DE3686247T2 DE3686247T2 DE8686118116T DE3686247T DE3686247T2 DE 3686247 T2 DE3686247 T2 DE 3686247T2 DE 8686118116 T DE8686118116 T DE 8686118116T DE 3686247 T DE3686247 T DE 3686247T DE 3686247 T2 DE3686247 T2 DE 3686247T2
- Authority
- DE
- Germany
- Prior art keywords
- dye
- formula
- dyeing
- monoazo
- monoazo dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 title claims description 115
- 239000000835 fiber Substances 0.000 title claims description 32
- 229920000728 polyester Polymers 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title description 8
- 238000004043 dyeing Methods 0.000 claims description 58
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 56
- 238000012986 modification Methods 0.000 claims description 41
- 239000013078 crystal Substances 0.000 claims description 22
- 230000004048 modification Effects 0.000 claims description 12
- 238000001228 spectrum Methods 0.000 claims description 10
- 238000002441 X-ray diffraction Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000000986 disperse dye Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000000463 material Substances 0.000 description 17
- 239000004744 fabric Substances 0.000 description 16
- -1 monoazo compound Chemical class 0.000 description 12
- 238000005299 abrasion Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000010979 ruby Substances 0.000 description 4
- 229910001750 ruby Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 3
- 238000009981 jet dyeing Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LVRZDVFALRTAHV-UHFFFAOYSA-N 2-(n-ethylanilino)ethyl benzoate Chemical compound C=1C=CC=CC=1N(CC)CCOC(=O)C1=CC=CC=C1 LVRZDVFALRTAHV-UHFFFAOYSA-N 0.000 description 1
- UJTRMFNKHYGXDI-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)anilino]ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(CCC#N)C1=CC=CC=C1 UJTRMFNKHYGXDI-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000009974 package dyeing Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60298484A JPS62158760A (ja) | 1985-12-30 | 1985-12-30 | モノアゾ染料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3686247D1 DE3686247D1 (de) | 1992-09-03 |
| DE3686247T2 true DE3686247T2 (de) | 1993-02-11 |
Family
ID=17860297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8686118116T Expired - Lifetime DE3686247T2 (de) | 1985-12-30 | 1986-12-29 | Mischung von monoazofarbstoffen und verfahren zuem faerben von polyester fasern unter verwendung derartiger farbstoffmischungen. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4734101A (enrdf_load_html_response) |
| EP (1) | EP0228092B1 (enrdf_load_html_response) |
| JP (1) | JPS62158760A (enrdf_load_html_response) |
| DE (1) | DE3686247T2 (enrdf_load_html_response) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH674987A5 (enrdf_load_html_response) * | 1986-08-01 | 1990-08-15 | Sandoz Ag | |
| IT1224790B (it) * | 1987-12-04 | 1990-10-24 | Sandoz Ag | Composti azoici, loro preparazione e loro impiego come coloranti dispersi. |
| DE3844067A1 (de) * | 1988-12-28 | 1990-07-05 | Bayer Ag | Mischungen von dispersionsazofarbstoffen |
| DE69006470T2 (de) * | 1989-11-22 | 1994-09-29 | Hoechst Mitsubishi Kasei | Wasserunlösliche Monoazofarbstoffe und deren Mischungen. |
| JPH0745636B2 (ja) * | 1991-06-18 | 1995-05-17 | 三菱化成ヘキスト株式会社 | 分散染料混合物 |
| TW324021B (en) * | 1994-03-08 | 1998-01-01 | Daistar Japan Kk | Mono-azo dyestuff |
| DE19726425A1 (de) * | 1997-06-23 | 1998-12-24 | Dystar Textilfarben Gmbh & Co | Färbestabiler Monoazofarbstoff, dessen Herstellung und Verwendung |
| CN1317337C (zh) * | 2004-12-28 | 2007-05-23 | 浙江龙盛集团股份有限公司 | 一种红色单偶氮染料组合物 |
| JP5236550B2 (ja) | 2009-03-30 | 2013-07-17 | 三菱電機株式会社 | 真空断熱材とその製造方法、及びこの真空断熱材を備えた断熱箱 |
| KR101722895B1 (ko) | 2013-12-30 | 2017-04-05 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 폴리티올, 불포화 화합물, 및 염료를 포함하는 조성물 및 그러한 조성물에 관련된 방법 |
| AU2014374132B2 (en) | 2013-12-30 | 2017-07-13 | 3M Innovative Properties Company | Dye, filler made therefrom, compositions including the filler, and method of determining degree of cure of such compositions |
| CN105440727B (zh) * | 2014-08-29 | 2017-09-22 | 浙江迪邦化工有限公司 | 一种带酯基偶氮分散染料的制备方法 |
| BR112017028509A2 (pt) | 2015-06-29 | 2018-08-28 | 3M Innovative Properties Co | composições incluindo um politiol, um composto insaturado e um corante, e métodos relacionados a tais composições |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1324235A (en) * | 1969-11-22 | 1973-07-25 | Yorkshire Chemicals Ltd | Monoazo benzthiazole disperse dyes |
| JPS5647450A (en) * | 1979-09-27 | 1981-04-30 | Nippon Kayaku Co Ltd | Preparation of fine particulate heat-resistant benzothiazole azo dye |
| DE3018028A1 (de) * | 1980-05-10 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2-amino-6-nitrobenzthiazol |
| JPS58129061A (ja) * | 1982-01-27 | 1983-08-01 | Sumitomo Chem Co Ltd | モノアゾ化合物の製造法 |
| DE3425127A1 (de) * | 1984-07-07 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe |
-
1985
- 1985-12-30 JP JP60298484A patent/JPS62158760A/ja active Granted
-
1986
- 1986-12-29 US US06/946,964 patent/US4734101A/en not_active Expired - Lifetime
- 1986-12-29 EP EP86118116A patent/EP0228092B1/en not_active Expired - Lifetime
- 1986-12-29 DE DE8686118116T patent/DE3686247T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0228092A3 (en) | 1989-10-11 |
| EP0228092B1 (en) | 1992-07-29 |
| US4734101A (en) | 1988-03-29 |
| DE3686247D1 (de) | 1992-09-03 |
| JPH0412903B2 (enrdf_load_html_response) | 1992-03-06 |
| EP0228092A2 (en) | 1987-07-08 |
| JPS62158760A (ja) | 1987-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DYSTAR JAPAN LTD., OSAKA, JP |